DE1518452C3 - 4 substituierte 2 Benzhydryl 2 butanol Derivate und Verfahren zu ihrer Herstellung - Google Patents
4 substituierte 2 Benzhydryl 2 butanol Derivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1518452C3 DE1518452C3 DE1518452A DE1518452A DE1518452C3 DE 1518452 C3 DE1518452 C3 DE 1518452C3 DE 1518452 A DE1518452 A DE 1518452A DE 1518452 A DE1518452 A DE 1518452A DE 1518452 C3 DE1518452 C3 DE 1518452C3
- Authority
- DE
- Germany
- Prior art keywords
- benzhydryl
- butanol
- substituted
- preparation
- dimethylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 benzhydryl 2 butanol derivatives Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 206010011224 Cough Diseases 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WQVAMFRPCWXWSS-UHFFFAOYSA-N 4-(dimethylamino)butan-2-one Chemical compound CN(C)CCC(C)=O WQVAMFRPCWXWSS-UHFFFAOYSA-N 0.000 description 3
- UXXAPTACMRJCDK-UHFFFAOYSA-N C=1C=CC=CC=1C([Li])C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C([Li])C1=CC=CC=C1 UXXAPTACMRJCDK-UHFFFAOYSA-N 0.000 description 3
- 230000000954 anitussive effect Effects 0.000 description 3
- 229960004126 codeine Drugs 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 2
- DGIMBNDDRDPDRK-UHFFFAOYSA-N 4-(dimethylamino)-2-methyl-1,1-diphenylbutan-2-ol Chemical compound CN(CCC(C)(O)C(C1=CC=CC=C1)C1=CC=CC=C1)C DGIMBNDDRDPDRK-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
- 229940124584 antitussives Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Chemical group 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229960004415 codeine phosphate Drugs 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VUTJNJCFZIUTGB-UHFFFAOYSA-N 4-(diethylamino)-2-methyl-1,1-diphenylbutan-2-ol 2,3-dihydroxybutanedioic acid Chemical compound C(=O)(O)C(O)C(O)C(=O)O.C(C)N(CCC(C)(O)C(C1=CC=CC=C1)C1=CC=CC=C1)CC VUTJNJCFZIUTGB-UHFFFAOYSA-N 0.000 description 1
- XLEOCTUCGZANAC-UHFFFAOYSA-N 4-(diethylamino)butan-2-one Chemical compound CCN(CC)CCC(C)=O XLEOCTUCGZANAC-UHFFFAOYSA-N 0.000 description 1
- SUVYXKDAVYFUMG-UHFFFAOYSA-N 4-aminobutan-2-one Chemical compound CC(=O)CCN SUVYXKDAVYFUMG-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 210000003801 laryngeal nerve Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US463059A US3395146A (en) | 1965-02-11 | 1965-02-11 | 4-substituted-2-benzhydryl-2-butanol derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1518452A1 DE1518452A1 (de) | 1972-03-09 |
| DE1518452B2 DE1518452B2 (de) | 1973-03-08 |
| DE1518452C3 true DE1518452C3 (de) | 1973-10-04 |
Family
ID=23838718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1518452A Expired DE1518452C3 (de) | 1965-02-11 | 1965-10-20 | 4 substituierte 2 Benzhydryl 2 butanol Derivate und Verfahren zu ihrer Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3395146A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1518452C3 (cg-RX-API-DMAC10.html) |
| DK (1) | DK119774B (cg-RX-API-DMAC10.html) |
| FR (1) | FR5166M (cg-RX-API-DMAC10.html) |
| GB (1) | GB1061306A (cg-RX-API-DMAC10.html) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3668206A (en) * | 1968-10-16 | 1972-06-06 | Venkatachala Lakshmi Narayanan | Heterocyclic amine derivatives of 5,8-dihydronaphthyloxy propanols |
| US3728379A (en) * | 1971-06-29 | 1973-04-17 | Lilly Co Eli | Propoxyphene salts |
| US3960960A (en) * | 1972-09-11 | 1976-06-01 | Chemie Linz Aktiengesellschaft | 1,1-Diphenyl-1-lower alkoxy-amino-alkanes and the salts thereof |
| US4101676A (en) * | 1973-02-24 | 1978-07-18 | Beecham Group Limited | Diphenylpropylamines to treat depression |
| GB1443441A (en) * | 1973-02-24 | 1976-07-21 | Beecham Group Ltd | Pharmaceutical compositions comprising diphenylpropanolamine deri vatives |
| US3987201A (en) * | 1974-12-24 | 1976-10-19 | Eli Lilly And Company | Method for treating arrhythmia |
| US4001328A (en) * | 1975-06-04 | 1977-01-04 | Eli Lilly And Company | Diarylbutanolamines |
| US4049827A (en) * | 1975-06-04 | 1977-09-20 | Eli Lilly And Company | Method of treating arrhythmia with diarylbutanolamines |
| FR2614021B1 (fr) * | 1987-04-14 | 1991-03-01 | Andre Buzas | Derives de la 1-((1,1-diphenyl)-1-alcenyl)-piperazine, procede d'obtention et compositions pharmaceutiques les contenant |
| US5001160A (en) * | 1988-04-28 | 1991-03-19 | Marion Laboratories, Inc. | 1-aryl-1-hydroxy-1-substituted-3-(4-substituted-1-piperazinyl)-2-propanones and their use in treatment of neurogenic bladder disorders |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1915334A (en) * | 1930-10-16 | 1933-06-27 | Du Pont | Fluosilicate of organic heterocyclic bases and process of making it |
| US2075359A (en) * | 1930-10-16 | 1937-03-30 | Du Pont | Insecticide |
| US3075014A (en) * | 1960-06-14 | 1963-01-22 | Richardson Merrell Inc | Basic substituted alkoxy diphenylalkanols, diphenylalkenes and diphenylalkanes |
-
1965
- 1965-02-11 US US463059A patent/US3395146A/en not_active Expired - Lifetime
- 1965-10-20 DE DE1518452A patent/DE1518452C3/de not_active Expired
-
1966
- 1966-01-24 GB GB3183/66A patent/GB1061306A/en not_active Expired
- 1966-02-08 FR FR48737A patent/FR5166M/fr not_active Expired
- 1966-02-09 DK DK66466AA patent/DK119774B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3395146A (en) | 1968-07-30 |
| GB1061306A (en) | 1967-03-08 |
| DK119774B (da) | 1971-02-22 |
| FR5166M (cg-RX-API-DMAC10.html) | 1967-06-19 |
| DE1518452A1 (de) | 1972-03-09 |
| DE1518452B2 (de) | 1973-03-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |